m-Chloroperbenzoic acid → 3-Chloromethyl-2-methyl-pyridine 1-oxide

HRID 1681

반응식

HRID 1681 반응식
[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:15]>C(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N+:5]([O-:15])[CH:6]=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 122437113-(Chloromethyl)-2-methylpyridine

생성물 1

HCID 220536063-Chloromethyl-2-methyl-pyridine 1-oxide

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a stirred solution of 3-chloromethyl-2-methylpyridine from Step 2 above (0.50 g; 3.5 mmol) in CHCl3 (40 mL) was added m-chloroperoxybenzoic acid (1.1 g of 55:45 mCPBA:mCBA; 3.5 mmol). After 1.5 h, TLC analysis indicated complete conversion to a lower Rf product. The solution was extracted with equal volumes of saturated aqueous NaHCO3 and water, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 3-Chloromethyl-2-methylpyridine N-oxide was obtained as a solid (TLC: Rf =0.30 (97:3 CH2Cl2 :MeOH); FAB MS m/z 158 (M+ +H)).

후처리

  1. extractionThe solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by pressurized silica gel column chromatography

출처 및 근거

ORD 기록
ord-b8dbba8e74ff4118bc3513f530757669
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726172

연결된 노트

불러오는 중…